Leelanau Peninsula Wineries Holiday Rentals

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Holiday Rentals in Leelanau Peninsula Wineries

Property grounds
Remodeled Leelanau Chalet home. Minutes from Sleeping Bear Dunes & Lakeshore.
10.0 out of 10, Exceptional, (21)
"We had a really great weekend on the Leelanau Peninsula! We all slept great in the comfy beds, and my partner enjoyed cooking in the really well stocked kitchen. There were all the utensils and pots and pans we needed, sharp knives, oil and vinegar and even fresh herbs from the garden. There were plenty of fresh clean linens. There was one day we didn't leave the property at all because there was enough beauty all around us. There were rare wildflowers (trillium and jack in the pulpit) and a...
The price is NZ$283
per night
19 Jun - 20 Jun
Remodeled Leelanau Chalet home. Minutes from Sleeping Bear Dunes & Lakeshore.
Property grounds
Love North Shore Cherry Cove Beachfront On West Grand Traverse Bay In Leelanau!
10.0 out of 10, Exceptional, (228)
"Our stay was great. Beautiful location. Very comfortable. Loved it!!! Hope to come back."
Love North Shore Cherry Cove Beachfront On West Grand Traverse Bay In Leelanau!
Exterior
Super cute loft on the lake!
10.0 out of 10, Exceptional, (3)
"All I can say I cried going home"
Super cute loft on the lake!
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Exterior
Quiet, Private, Waterfront - Luxury on 125 Ft. of Suttons Bay
10.0 out of 10, Exceptional, (99)
"Location Location Location Quaint Quiet Cozy Place"
Quiet, Private, Waterfront - Luxury on 125 Ft. of Suttons Bay
Property grounds
Walk to everything from this 1 Bedroom Beach House
10.0 out of 10, Exceptional, (18)
"Nice time of year to be up there, the town was very sleepy. Enjoyed the scenery and hiking."
Walk to everything from this 1 Bedroom Beach House
Exterior
Wayfarer Tree House S
10.0 out of 10, Exceptional, (3)
"Great communication about property and surrounding area. Well equipped kitchen but microwave on top of refrigerator, very high. Great fire ring outside and close walk to lake. Nice shower upstairs but also need shower downstairs as tub inaccessible for most seniors. Windows everywhere so felt we were living in the woods."
The price is NZ$1,294
per night
23 May - 24 May
Wayfarer Tree House S
Beach nearby, sun-loungers, beach towels
Leelanau condo on golf course close to beaches, wineries, sand dunes, and more
10.0 out of 10, Exceptional, (81)
"There was a slight odor of pine (I think) which I found offensive because I am super sensitive to scents. It was especially annoying when trying to fall asleep. Other than that, the condo is neat & well supplied for the small condo."
Leelanau condo on golf course close to beaches, wineries, sand dunes, and more
Sun-loungers
Waterfront Home with Dock On Lake Leelanau Near Beaches, Wineries, Hikes
10.0 out of 10, Exceptional, (112)
"This house was great for our family, lots of space to spread out, great location to get to other spots in leelanau and also traverse city. Would definitely recommend!"
Waterfront Home with Dock On Lake Leelanau Near Beaches, Wineries, Hikes
Beach nearby
Secluded Suttons Bay Abode w/ Fire Pit, Near Lakes
10.0 out of 10, Exceptional, (2)
"We were up for a quick weekend in and around Suttons Bay. This location was comfortable and served our needs perfectly. Thanks."
Secluded Suttons Bay Abode w/ Fire Pit, Near Lakes
Smart TV, fireplace, table football, books
Leelanau High 5 at Sugar Loaf Mountain!
10.0 out of 10, Exceptional, (9)
"The property was in a great location and convenient to all areas around Traverse City. The bedrooms were comfortable, the child safety gates were helpful, they even provided a pack ‘n play last minute for us. The only downside of the stay/location is that the pool was listed as heated and open through Labor Day. The pool was open and even though there were days of 85+ degree weather, it was not heated and this not usable; areas of Lake Michigan were actually warmer. Other than that, I would...
Leelanau High 5 at Sugar Loaf Mountain!
Aerial view
Aaron's Fun House
10.0 out of 10, Exceptional, (2)
"The house was perfect for our stay. The kids had their own rooms with television. It could use more hot water."
Aaron's Fun House
Beach nearby, sun-loungers
Homestead condo, Beautiful view of Lk MI & Manitou Is , A/C. internet & cable.
10.0 out of 10, Exceptional, (179)
"We love staying at the Homestead, and this location didn't disappoint! The views from the living room and master bedroom were very beautiful, especially since the leaves on the trees hadn't quite come in yet during our early May stay. We also appreciated that there were relatively few steps to climb to the condo from the parking lot compared to the last Homestead condo we stayed in, which had over 80 steps. The condo also had everything we needed, and we know that a summer visit someday will be...
Homestead condo, Beautiful view of Lk MI & Manitou Is , A/C. internet & cable.
Beach
Modern home in Glen Arbor. Steam shower. Walk to lake. Air conditioning.
10.0 out of 10, Exceptional, (30)
"Property is everything and more. We had a fun winter getaway!"
Modern home in Glen Arbor. Steam shower. Walk to lake. Air conditioning.
Exterior
~ Lakefront Pickleball Home ~
10.0 out of 10, Exceptional, (13)
"Beautiful place, weather, lake and community. We will be back!!"
~ Lakefront Pickleball Home ~
Property grounds
After Dune Delight 5BR Home River Kayaks Beaches
9.8 out of 10, Exceptional, (16)
"This property was home to our group of 8 golfers this past weekend. All of the guys really enjoyed the setting. Fishing from the dock. Paddling the kayaks on the Crystal River. Sitting around the campfire. Watching the big TV in the family room. Eating meals in the screened-in porch while overlooking the river. This is an expansive house with plenty of room for everyone to enjoy. Book it now. You will love it. Communication with the property manager (Dylan) was excellent. Very speedy...
After Dune Delight 5BR Home River Kayaks Beaches
Property grounds
Quiet and Comfy 3 bed/2bath - Chalet w/ Hot tub
9.8 out of 10, Exceptional, (16)
"Great stay! Property was quaint, home was clean and welcoming. We absolutely loved the hot tub and used it daily. Centrally located for the peninsula."
Quiet and Comfy 3 bed/2bath - Chalet w/ Hot tub
Property grounds
Riverfront condo with beach access to lake, fireplace, furnished deck & cable
9.8 out of 10, Exceptional, (16)
"nice view"
Riverfront condo with beach access to lake, fireplace, furnished deck & cable
Property grounds
Time to rest and enjoy nature
9.6 out of 10, Exceptional, (10)
"The apartment was very spacious, and the view of the bay was spectacular. I would highly recommend this place to friends and family."
Time to rest and enjoy nature
Aerial view
Center of Leelanau County. Extended Stay Winter 23/24 And Short Term Summer 2024
9.6 out of 10, Exceptional, (86)
"Our family enjoyed staying here over Labor Day weekend! We found the house to be clean and with enough room to accommodate everyone. The location is great with so many different beaches and restaurants nearby. It was quiet at night and cool enough with just the windows open. We would stay here again!"
Center of Leelanau County. Extended Stay Winter 23/24 And Short Term Summer 2024
Fridge, microwave, oven, stovetop
Beach Access!! Close to Traverse city and Sutton’s bay.
9.6 out of 10, Exceptional, (44)
"Place was clean and had everything we needed for our group. Would stay there again."
Beach Access!! Close to Traverse city and Sutton’s bay.
Don't see what you're looking for?
See all available properties in Leelanau Peninsula Wineries
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Leelanau Peninsula Wineries you may be interested in

Property grounds
Love North Shore Cherry Cove Beachfront On West Grand Traverse Bay In Leelanau!
10.0 out of 10, Exceptional, (228)
"Our stay was great. Beautiful location. Very comfortable. Loved it!!! Hope to come back."
Love North Shore Cherry Cove Beachfront On West Grand Traverse Bay In Leelanau!
Property grounds
After Dune Delight 5BR Home River Kayaks Beaches
9.8 out of 10, Exceptional, (16)
"This property was home to our group of 8 golfers this past weekend. All of the guys really enjoyed the setting. Fishing from the dock. Paddling the kayaks on the Crystal River. Sitting around the campfire. Watching the big TV in the family room. Eating meals in the screened-in porch while overlooking the river. This is an expansive house with plenty of room for everyone to enjoy. Book it now. You will love it. Communication with the property manager (Dylan) was excellent. Very speedy...
After Dune Delight 5BR Home River Kayaks Beaches
Exterior
Leelanau Sands Casino & Lodge
2.5 star property
8.2 out of 10, Very good, (322)
"I would highly recommend this resort. It was a perfect getaway."
The price is NZ$326
per night
29 May - 30 May
Leelanau Sands Casino & Lodge
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Leelanau Peninsula Wineries holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Leelanau Peninsula Wineries. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Leelanau Peninsula Wineries. Seeing all the best attractions is bound to make you fall in love with Leelanau Peninsula Wineries. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Leelanau Peninsula Wineries short-term rentals, that won’t be hard to do.